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Stephens City Holiday Rentals

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Our top choices for Stephens City holiday rentals

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2)
"Small but appropriately priced."
United States
John M.
The price is NZ$330
includes taxes & fees
1 Jan - 2 Jan 2026
Rosamond nice downtown studio apt

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
2.0 star property
Winchester Historic District
8.6 out of 10, Excellent, (4)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
United States
matthew r.
The price is NZ$394
includes taxes & fees
30 Dec - 31 Dec
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (12)
"Property was just what we were looking for "
United States
Tim C.
The price is NZ$380
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain View Bungalow in Front Royal

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
2.0 star property
Winchester Historic District
6.0 out of 10, (1)
The price is NZ$340
includes taxes & fees
30 Dec - 31 Dec
The Stock Exchange downtown 3rd floor studio apt

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6)
"The home was exactly as advertised! It was also located in a great spot whichbwas within walking distance to many of the Historic District of Downtown Winchester. We will definitely be staying here again!"
United States
David K.
The price is NZ$604
includes taxes & fees
30 Dec - 31 Dec
Cameron Charmer pristine downtown apt with double master suites

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
2.0 star property
Stephens City
10.0 out of 10, Exceptional, (1)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is NZ$281
includes taxes & fees
1 Jan - 2 Jan 2026
Luxury tiny home farm stay on historic property with hot tub in Stephens City

Big Sunny Family House

Big Sunny Family House
Front Royal
10.0 out of 10, Exceptional, (40)
"Wonderful house and town! Loved every minute of our trip! "
United States
MaryAnn G.
The price is NZ$713
includes taxes & fees
27 Jan - 28 Jan 2026
Big Sunny Family House

Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (14)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is NZ$575
includes taxes & fees
30 Dec - 31 Dec
Nostalgia Lane in the heart of the city

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (1)
"Beautiful space; helpful host."
United States
Sally C.
The price is NZ$674
includes taxes & fees
1 Jan - 2 Jan 2026
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (6)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is NZ$615
includes taxes & fees
30 Dec - 31 Dec
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (5)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
United States
Stephanie L.
The price is NZ$668
includes taxes & fees
30 Dec - 31 Dec
Scarborough Fair walk to downtown two story apt

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (55)
"It was a beautiful getaway from all of the busy mess from our normal lives"
United States
Tailor N.
The price is NZ$462
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Retreat - Hot tub + Mountain Views + Pets

Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (8)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
The price is NZ$650
includes taxes & fees
4 Jan - 5 Jan 2026
Aslan's How - Cabin with Valley Views & Hot Tub!

Peaceful Retreat on Creekside

Peaceful Retreat on Creekside
Edinburg
9.6 out of 10, Exceptional, (15)
"Amazing location that was perfect for a weekend getaway! The creek was so peaceful and water views from the deck were amazing! "
United States
Richard D.
The price is NZ$360
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful Retreat on Creekside

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (31)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
The price is NZ$648
includes taxes & fees
5 Jan - 6 Jan 2026
Rebels Rest - Cabin with Enchanting Sunset Views!

Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
10.0 out of 10, Exceptional, (63)
"Comfortable, clean, welcoming, wonderful hot tub, great view from the porch!"
United States
Carol M.
The price is NZ$629
includes taxes & fees
4 Jan - 5 Jan 2026
Blue Ridge Getaway - Sunset Views, A.T. Access

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (5)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
United States
Vinod B.
The price is NZ$769
includes taxes & fees
5 Jan - 6 Jan 2026
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Harpers Ferry
10.0 out of 10, Exceptional, (83)
"This is a super cute mountain cabin that has been completely redone with some pretty high end finishes. Our family thoroughly enjoyed our quick visit!"
United States
Sara S.
The price is NZ$490
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
10.0 out of 10, Exceptional, (16)
"Great location. Great house. Could not have asked for more. "
United States
A. Bland and D. T.
The price is NZ$671
includes taxes & fees
4 Jan - 5 Jan 2026
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (31)
"Great location. Beautiful scenery. House was clean."
United States
Brandon H.
The price is NZ$624
includes taxes & fees
14 Jan - 15 Jan 2026
Peaceful Lakefront Cottage with Mountain Views!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Stephens City Hotel Reviews

Find out more about Stephens City

Everything you need to know about Stephens City holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stephens City holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stephens City holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stephens City holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stephens City. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stephens City holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stephens City holiday rentals we have selected for you start as low as NZ$462 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stephens City rentals

At Expedia, we put the best Stephens City holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Stephens City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stephens City holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stephens City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Stephens City?

Yes, there are holiday rentals in Stephens City close to Appleland Sports Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Stephens City has a good selection of restaurants. Make sure you have time to check out the shopping and wineries during your trip.

What are some of the best holiday rentals that Stephens City has to offer?

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub: This holiday home rental outside of Stephens City is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Stephens City?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Stephens City stay.

What’s there to see and do in Stephens City?

While exploring the area, visit family-friendly sights like Appleland Sports Center, or get outside and enjoy nature at Shenandoah River. In the wider area, you’ll find Valerie Hill Winery and Dinosaur Land.

What’s a holiday rental in Stephens City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stephens City. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.